Take That Crowdfunding Cynics! Rally Raises Largest AngelList Deal Ever

It's not every day you get 200 emails in a single hour, offering you money.

But on May 15, Tom Serres had electronic bling flying at him from all angles. And it just kept coming. He could barely keep up. His assistant quickly dropped everything and for eight straight days entered thousands and thousands of offers of cash into a spreadsheet.

We're not talking about offers from Nigerian princes, if you help break their dads out of jail. We're talking about accredited investors from around the globe. We're talking about name brands like Bebo founder Michael Birch, Digg founder Kevin Rose, and epic self-promoter Tim Ferris, the kind of people you'd actually want money from. Talk about a good problem to have.

Serres is typically the guy helping others raise money. He is the founder and CEO of Rally, a site that helps a very long tail of causes raise money via the Web. By "causes," think everyone from Mitt Romney to a Costa Rican kid raising money to go to Cornell. And by "help," think more than just pinging your friends over Facebook and Twitter to contribute.

Rally works almost as if a content management system and PayPal had a baby, and raised that baby to love campaigns and nonprofits and other worthy things that (arguably) need donations. It helps groups tell an impactful story and shows powerful analytics of how that heart string tugging turns into revenues. And then, it handles the payments.

While a lot of cause-related apps are all about democratizing the long tail of would-be contributors (Think: making it more efficient to donate to the Red Cross), Rally focuses on the long tail of causes (Think: a neighborhood park that needs a new swing set.)

It is incredibly non-judgemental about what a "cause" even is. They don't have to agree with you. You don't have to be a 501(c)(3). You just can't be a fraudster. Serres once gave $20 to a girl wanting to go to Comic Con. She drew a picture of him riding a unicorn in exchange. "If you're working for Barack Obama, you have a team to A/B test everything and look at the analytics," says Serres, who cut his teeth working for politicians in Texas. "The average person raising money for the park doesn't have that."

So far, 1.4 million users have raised hundreds of millions of dollars for some 14,000 causes. Rally takes a fee slightly larger than PayPal's for its trouble, but it's also delivering a lot more value on the content management and analytics side.

And as you may have read yesterday, the company now has some $7.9 million more to help it do that, during the pivotal upcoming election year. What you haven't read about is how Rally raised that whopper of a round. And it's a story that has huge implications for anyone building a company, and the entire debate about recently approved crowd funding aspects of the JOBS Act.

Serres had two big name investors in Greylock's Reid Hoffman and Floodgate's Mike Maples. They'd already invested in the seed round back in 2009 and were ready to re-up. He could have just marched up and down Sand Hill Road, dropping their names and he likely would have been fine. That's the way it's been done since the days of Intel and Apple, when those pastoral offices on Sand Hill Road were actually examples of modern architecture.

Instead he decided to do something a little radical. He called Naval Ravikant of AngelList and asked if anyone had ever raised a full-on Series A via the site. Serres wanted to put his desired-money where his mouth was and raise the cash online -- just like his causes do on Rally.

Ravikant's whole mission is to drag that stealthy Sand Hill Road death-march-with-PowerPoints out of the conference rooms and into the light of day. It's a movement that investors find terrifying, abhorrent, exhilarating, and promising -- depending on which of the investors you speak with. Many feel a mixture of all of the above.

That's why Ravikant was one of the main drivers behind pushing the JOBS Act through congress -- so everyone could legally raise money this way. "He got the law changed," said Ben Horowitz of Andreessen Horowitz at PandoMonthly last week. "Like... Go Naval! That was awesome. He went to Washington... And I mean, he's just, like, a guy. Like one of us. And he's like, 'I got to get this done,' and went to Washington with Steve Case, and they changed the law. That blew my mind."

Not everyone is so thrilled. Indeed our staffers and contributors have spilled plenty of ink on why no company of any repute would raise money this way. Rally just proved them all wrong.

Ravikant says companies have raised Series A rounds on the site on AngelList, but only a handful, never with big name investors like that and none came close to the $7.9 million amount. As far as anyone involved in the deal knows, it was the largest round ever raised online.

Serres spent eight full days traveling, meeting, and talking on the phone. Thousands of meals were weeded down to 70 meetings and 18 investors were selected from around the world. He says it was the hardest thing he's ever done, and that's saying something: Serres was a single dad in the early bootstrapped days of the company. The both motley and star-studded syndicate included a tech magnate from Beirut. "I've never met him! I've never even seen his face! But I'm going to go to Beirut, and it's going to be awesome," Serres says.

$4.4 million of the round came from AngelList -- millions more than he expected to raise. "I had no time to eat, sleep, or even move," Serres says. For eight days it consumed every ounce of his time and energy. But then it was done. It was both intense and efficient at once.

But it was more than just an efficient way to raise money. It was essentially a mini-IPO -- with all the marketing pop an IPO entails. Thousands of people heard the Rally story over the course of the fundraising -- way more than would have if he were just pitching the top firms of Silicon Valley. And each of his investors agreed to blog about why they funded Rally.

I can only imagine Ravikant watching it all unfold with a Cheshire Cat grin. This wasn't merely about a different way to raise funds. Money was the least of what Rally got out of this experience. "This totally cemented my core belief that this is the way the world is going," Serres says. It just so happens to be the same belief that underlies Rally.

"Rally felt like the perfect set of circumstances to test if this could work," Maples said. "Reid was willing to step up and do it with me. We put in the money and said here are the terms. Let's make a run at it. I want to be one of the people in the industry who is an activist, who tries to create more and more options for entrepreneurs. As an investor you can try to increase your power vis a vis entrepreneur, but I think that's a fool errand. The world has changed."

Of course, not all companies are suited for this...at all. For one thing, Rally was undeniably helped out by the fact that two very name brand investors were already leading the round. There are a world of people who would happily pile in with Mike Maples and Reid Hoffman, no matter what they were funding. Those aren't always the people you want in your company. Likewise a consumer-friendly story and traction helped. You can't imagine, say, a new enterprise software company getting this much of a buzzy reaction. "It's hard to say if I'm an outlier or not," Serres says. "The idea that companies are going to raise $1 million with $25 dollar investments at a time... I just don't see that happening."

Ravikant adds an important caution of his own: "I just hope they make their investors money." In venture world, it's not a happy story until the exit.